α-Sulfenylalkylation of carbonyl compounds at the α-position via magnesium amide-induced enamine sulfenylalkylation with sulfoxides

✍ Scribed by Kazuhiro Kobayashi; Masataka Kawakita; Susumu Irisawa; Hideki Akamatsu; Kouji Sakashita; Osamu Morikawa; Hisatoshi Konishi

• Book ID: 104209129
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 430 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)83005-6

✦ Synopsis

The reactions of enamines with sulfoxides bearing a-hydrogens in the presence of a magnesium amide, generated in situ from the reaction of ethylmagnesium bromide with diisopropylamine. afforded the corresponding a-sulfenylalkylated ketones and aldehydes in isolated yields ranging from 39 to 76%. This procedure was successfully extended to the bis(metbylthio)methylation with methyl (methylthio)methyl sulfoxide.